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[ CAS No. 915213-54-6 ] {[proInfo.proName]}

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Chemical Structure| 915213-54-6
Chemical Structure| 915213-54-6
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Product Details of [ 915213-54-6 ]

CAS No. :915213-54-6 MDL No. :MFCD18909256
Formula : C10H16F2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GZWGGXBBJGJHBC-UHFFFAOYSA-N
M.W : 206.23 Pubchem ID :59304597
Synonyms :

Calculated chemistry of [ 915213-54-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.49
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.56
Log Po/w (XLOGP3) : 2.55
Log Po/w (WLOGP) : 3.61
Log Po/w (MLOGP) : 2.48
Log Po/w (SILICOS-IT) : 2.91
Consensus Log Po/w : 2.82

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.713 mg/ml ; 0.00346 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.367 mg/ml ; 0.00178 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.362 mg/ml ; 0.00175 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 915213-54-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 915213-54-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 915213-54-6 ]
  • Downstream synthetic route of [ 915213-54-6 ]

[ 915213-54-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 915213-54-6 ]
  • [ 915030-40-9 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #2: With hydrogenchloride In water
The compound 223e (3.2 g, 15.5 mmol) was dissolved in MeOH (5 ml) and treated with LiOH (559 mg, 23.3 mmol) overnight. The reaction mixture was acidified by 3 N HCl to pH 4 and extracted with CH2Cl2. The extract was dried over Na2SO4 and concentrated to afford 223f as brown oil (3 g, 100percent).
Reference: [1] Patent: US2006/264489, 2006, A1, . Location in patent: Page/Page column 78
[2] Patent: US2013/183269, 2013, A1, . Location in patent: Paragraph 1216; 1217
[3] Patent: US2015/23913, 2015, A1, . Location in patent: Paragraph 1461-1462
[4] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 517; 518
[5] Patent: WO2006/122200, 2006, A1, . Location in patent: Page/Page column 53
  • 2
  • [ 58012-34-3 ]
  • [ 915213-54-6 ]
YieldReaction ConditionsOperation in experiment
62% With diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 3 h; The compound 223d (4.6 g) was dissolved in CH2Cl2 (10 ml) and treated with diethylaminosulfur trifluoride (DAST, 5 ml) at room temperature for 3 hours. The reaction mixture was poured into ice/water (30 ml) and extracted with CH2Cl2. The extract was washed with satd. aqueous NaHCO3, brine, dried over Na2SO4 and concentrated to afford 223e as brown oil (3.2 g, 62percent).
0.4 g With ethanol; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 20℃; for 16 h; To a solution ofethyl 2-(4-oxocyclohexyl)acetate(0.4 g) inDCM(5 mL) was addedDeoxo-Fluor®(0.881 mL) andEtOH(0.038 mL). The reaction mixture was stirred at rt for 16 h and then diluted with sat. NaHCO3and EtOAc. The organic phase was washed with water, sat. NaCl and dried over anhydrous Na2SO4, filtered and dried to yield ethyl 2-(4,4-difluorocyclohexyl)acetate (0.4 g). To a solution ofethyl 2-(4,4-difluorocyclohexyl) acetateinTHF/MeOH(2 mL) was added 1NNaOH(1 mL), and the reaction mixture was stirred at rt for 16 h. The reaction mixture was concentrated, then diluted with EtOAc and acidified with 1N HCl. The organic phase was washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated to yield2-(4,4-difluorocyclohexyl)acetic acidas ayellowsolid.1H NMR (400 MHz, DMSO-d6) ppm 12.13 (1H, br. s.), 2.06-2.28 (3H, m), 1.92-2.03 (1H, m), 1.72-1.91 (4H, m), 1.31-1.48 (1H, m), 1.10-1.31 (2H, m).
Reference: [1] Patent: US2006/264489, 2006, A1, . Location in patent: Page/Page column 78
[2] Patent: WO2010/103429, 2010, A1, . Location in patent: Page/Page column 34-35
[3] Patent: US2013/183269, 2013, A1, . Location in patent: Paragraph 1216; 1217
[4] Patent: US2015/23913, 2015, A1, . Location in patent: Paragraph 1461-1462
[5] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 517; 518
[6] Patent: WO2006/122200, 2006, A1, . Location in patent: Page/Page column 52
  • 3
  • [ 1283719-20-9 ]
  • [ 915213-54-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8321 - 8336
  • 4
  • [ 22515-18-0 ]
  • [ 915213-54-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8321 - 8336
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